Month: September 2021

Adding a certain compound to certain chemical reactions, such as: 58971-11-2, name is 3-Bromophenethylamine, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 58971-11-2, Application In Synthesis of 3-Bromophenethylamine

General procedure: Toa solution of 2a (20.0 g, 0.1 mol)and triethylamine (30.3 g, 0.3 mol) in DCM (350 mL) was added ethylchloroformate (12.9 g, 0.1 mol) dropwise at 0 oC and then stirred atroom temperature for 3 h. The reaction mixture was washed with 3M HCl (100 mL×2), dried over Na2SO4 and concentrated under reducedpressure. The residue was purified by silica gel column chromatography (PET/EA= 25:1, v/v) to afford compound 3a as colorless oil (22.3 g, 82.0%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromophenethylamine, and friends who are interested can also refer to it.

Reference:
Article; Sun, Zhaozhu; Zhou, Tian; Pan, Xuan; Yang, Ying; Huan, Yi; Xiao, Zhiyan; Shen, Zhufang; Liu, Zhanzhu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3050 – 3056;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 4885-18-1

Dimethylamine 49 (1.31 g, 6.13 mmol) was dissolved in anhydrous THF (15 ml) under Ar(g) in a flame-dried round-bottomed flask equipped with a reflux condenser. To facilitate generation of the Grignard reagent, a catalytic amount of 12 was added to the solution. Crushed magnesium turnings (223 mg, 9.2 mmol) were then added to this solution, and the resulting solution was heated at reflux for 2 hr to generate the Grignard reagent. In a separate flamed-dried flask, diethyl phosphite (237 mul, 1.84 mmol) was dissolved in anhydrous THF (1.0 ml), and cooled to 0 C. with an ice bath. The solution of Grignard reagent was added dropwise to this solution, and the resulting solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was then quenched with water (1 ml), and the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, and the resulting solution was washed with water and brine. The combined organic extracts were dried over anhydrous MgSO4(s) and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, 20% v/v MeOH in CH2Cl2) to give phosphine oxide 50 as a colorless oil in 66% yield. 1H NMR (CDCl3, 400 MHz) delta 8.06 (d, J=1.2 Hz, 1H), 7.69 (s, 1H), 7.66 (s, 1H), 7.58 (t, J=7.5 Hz, 2H), 7.54 (dd, J=8.9, 1.2 Hz 2H), 7.45 (dd, J=7.6, 3.1 Hz 2H), 3.45 (s, 4H), 2.22 (s, 12H) ppm; 13C NMR (CDCl3, 100.6 MHz) delta 140.22 (d, J=10.7 Hz), 133.45, 132.15, 131.31 (d, J=12.2 Hz), 129.67 (d, J=11.2 Hz), 129.14 (d, J=12.2 Hz), 64.06, 45.58 ppm; 31P NMR (CDCl3, 161 MHz) delta 22.02 ppm; MS (ESI) m/z 288.0393 (MH+[C18H25N2OPH+]=288.0383).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4885-18-1, its application will become more common.

Reference:
Patent; Wisconsin Alumni Research Foundation; Raines, Ronald T.; Tam, Annie; Soellner, Matthew B.; US8410247; (2013); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 656-64-4, name is 3-Bromo-4-fluoroaniline, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 656-64-4, HPLC of Formula: C6H5BrFN

Compound III (63.0g, 387.5mmol) and ethanol (300 mL) was added 1L three-necked flask, dissolved under stirring, 3-bromo-4-fluoroaniline (81.0g, 426.3mmol), was added dropwise at room temperature NaHCO3(81.4g, 969.1mmol) was dissolved in 250mL of water was added, was warmed to 60 , reaction was 12 hours (complete reaction was monitored by TLC); and the reaction solution was transferred to a 1L round-bottom flask, ethanol was evaporated under reduced pressure, the residue was The organic layer was extracted three times with ethyl acetate (200mL × 3) were combined, washed twice with saturated NaCl solution, dried over anhydrous Na2SO4Drying; filtration, the filtrate was concentrated under reduced pressure to dryness, ethyl acetate / hexane to, filtration, and drying 45 deg.] C to give 76.0 g white solid, a yield of 62.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; China Pharmaceutical University; Zhu Qihua; He Guangchao; Dong Zhongxia; Shan Jinxi; Wang Junjie; Xu Kexin; Xu Yungen; (11 pag.)CN108101899; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 2,6-Dibromoaniline

A. 4-Bromo-7-nitrobenzofurazan (422A) To a solution of 2,6-dibromoaniline (1.0 g, 4.0 mmol) in CHCl3 (8 mL) was added a suspension of mCPBA (70% by HPLC, 1.4 g, 8.0 mmol) in CHCl3 (8 mL) and the resulting mixture was stirred for 24 h at rt. The reaction mixture was diluted with CHCl3 and washed successively with 2% Na2S2O3 solution, 5% Na2CO3 solution and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to leave a solid, which was suspended, into DMSO (15 mL). To this suspension was added a solution of NaN3 (272 mg, 4.19 mmol) in DMSO (15 mL) at rt. The resulting mixture was stirred at rt until most of the nitrogen had evolved and was then quickly heated to 120 C. for 3 min. The reaction mixture was cooled and poured onto crushed ice (100 g). After standing for 1 h the precipitates were filtered off, dried in vacuo and redissolved in conc. H2SO4 (5 mL). To this solution was added a solution of NaNO3 (400 mg, 4.7 mmol) in 50% H2SO4 (1.6 mL) and the temperature was maintained at 60 C. After the addition was complete, the mixture was heated at 85 C. for 30 min, cooled to rt and poured onto crushed ice (40 g). EtOAc was added, the layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to leave a solid which was purified by flash chromatography (silica gel, EtOAc (20%) in hexanes) affording compound 422A (785 mg, 81%) as a tan solid.

The synthetic route of 2,6-Dibromoaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Salvati, Mark E.; Balog, James Aaron; Pickering, Dacia A.; Giese, Soren; Fura, Aberra; Li, Wenying; Patel, Ramesh N.; Hanson, Ronald L.; Mitt, Toomas; Roberge, Jacques Y.; Corte, James R.; Spergel, Steven H.; Rampulla, Richard A.; Misra, Raj N.; Xiao, Hai-Yun; US2004/77605; (2004); A1;; ; Patent; Salvati, Mark E.; Mitt, Toomas; Patel, Ramesh N.; Hanson, Ronald L.; Brzozowski, David; Goswami, Animesh; Chu, Linda Nga Hoong; Li, Wen-sen; Simpson, James H.; Totleben, Michael J.; He, Weixuan; US2005/119228; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 43204-63-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 43204-63-3 as follows.

EXAMPLE 1 A mixture of 5-aminooxindol (14 g), 29 g of bis(beta-bromoethyl)amine.hydrobromide in 250 ml of ethanol was stirred under reflux for 8 hours and allowed to stand overnight at room temperature. To the mixture was added sodium carbonate (10.1 g) and the mixture was stirred further for 8 hours under reflux. After cooling to room temperature, crystals which precipitated were collected by filtration and recrystallized from a mixture of water and ethanol to give 16 g of 5-(1-piperazinyl)oxindol.hydrobromide. Pale yellow powdery crystal NMR (200 MHz, DMSO-d6) delta: 3.30 (8H, s), 3.47 (2H, s), 6.78 (1H, d, J=8.5 Hz), 6.90 (1H, dd, J=8.5 Hz, 2 Hz), 7.04 (1H, d, J=2 Hz), 8.88 (2H, brs), 10.27 (1H, s)

According to the analysis of related databases, 43204-63-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US4737501; (1988); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 553-94-6,Some common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

K3PO4 (212 mg, 1 mmol),aryl halides (0.5mmol) and phenylboronicacid (0.75 mmol) were added successively into a dried Schlenk tubewith a magnetic bar under nitrogen. Then a N,N-dimethylacetamide (DMA 0.05 mL) solution of tetraphosphine TPPDA (0.0005 mmol) andPdCl2 (0.0005 mmol), which was reacted at 100 C for 1 h prior to use,was added into the mixture. Afterwards, o-xylene (3 ml) was addedwith syringe. After being stirred for the required time in the preset con-ditions, the reaction mixture was cooled to room temperature. The mix-ture solution was extracted with ethyl acetate (3 5 mL). Combinedorganic phase was washed with brine (3 5 mL) and dried over anhy-drous MgSO4. The dried solution was ltered and puried by silica gelchromatography (petroleum ether 60-90 C) to give a correspondingproduct. Reaction condition: aryl halides 0.5 mmol, phenylboronic acid 0.75 mmol, K3PO4 1.0mmol, o-xylene 3 mL, catalyst PdCl2/TPPDA = 1/1, 90 C, under nitrogen, GC yields.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Dimethylbromobenzene, its application will become more common.

Reference:
Article; Guo, Fei-Chen; Zhou, Rong; Jiang, Zhi-Jie; Wang, Wei; Fu, Hai-Yan; Zheng, Xue-Li; Chen, Hua; Li, Rui-Xiang; Catalysis Communications; vol. 66; (2015); p. 87 – 90;,
Bromide – Wikipedia,
bromide – Wiktionary

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 626-88-0, name is 1-Bromo-4-methylpentane, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-4-methylpentane

To a solution of the 1H-indazol-5-ol (100 mg, 0.745 mmol) obtained in Reference Example 4 in N,N-dimethylformamide (2 ml) were added 1-bromo-4-methylpentane (0.109 ml, 0.745 mmol), tetrabutylammonium iodide (28 mg, 0.1 mmol) and potassium carbonate (103 mg, 0.745 mmol), and the resulting mixture was heated to 60C. After 9 hours, the mixture was poured into water (20 ml) and extracted with ethyl acetate (20 ml x 2). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 5-[(4-methylpentyl)oxy]-1H-indazole (60 mg, 37%). Melting point: 124-126C

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; EP1403255; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-5-(trifluoromethyl)aniline

To a solution of 3-Amino-5-bromobenzotrifluoride (200mg) in pyridine (2mL) was added methane sulphonyl chloride (115mg) and one crystal of 4-(dimethyl- amino) pyridine. The mixture was stirred at room temperature for four hours then diluted with ethyl acetate (50mL) and washed with HCI .(2M, 50mL) and saturated sodium chloride solution (50mL). Organics were separated, dried over sodium sulphate, filtered, and solvent was removed under reduced pressure to yield N-(3- bromo-5-trifluoromethyl-phenyl) -methanesulfonamide (264mg). ¹H NMR (MeOD); 6 7.59 (s, 1 H), 7.58 (s, 1 H), 7.40 (s, 1 H), 7.00 (s, 1 H), 3.11 (s, 3H). MS m/z 318.9 (M+1).

The synthetic route of 54962-75-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AKZO NOBEL N.V.; WO2005/121106; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 142808-15-9, name is 4-Bromo-2-fluorobenzotrifluoride belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Bromo-2-fluorobenzotrifluoride

0.4 g of t-butoxysodium, 13.7 mg of Pd2(dba)3, and 17.7 mg of 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl were added to 11 ml of toluene solution containing 1 g of the free form of the compound (F) obtained above and 0.73 g of 4-bromo-2-fluorobenzotrifluoride and the entire mixture was refluxed overnight under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. After being washed with water and dried with anhydrous magnesium sulfate, the organic layer was filtered and then vacuum-concentrated. The residue was purified by column chromatography (developing solution: mixed solvent of n-hexane and ethyl acetate) to obtain 0.54 g of the target compound. Viscous oil 1H-NMR(CDCl3, deltappm):1.08(t, 3H), 1.81-1.97(m, 4H), 2.04-2.23(m, 4H), 2.45(q, 2H), 3.97(t, 2H), 4.19(brs, 2H), 4.57(brt, 1H), 6.44-6.51(m, 2H), 6.76(d, 1H), 7.13(s, 1H), 7.16(d, 1H), 7.38(t, 1H)

The synthetic route of 142808-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIPPON SODA CO., LTD.; HAMAMOTO, Isami; TAKAHASHI, Jun; YANO, Makio; KAWAGUCHI, Masahiro; HANAI, Daisuke; IWASA, Takao; EP1932844; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 3972-64-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1-bromo-3-(tertbutyl)benzene (300 mg, 1.41 mmol) was dissolved in dry THF (5 mL) at -78 C under nitrogen and was stirred for 10 min. n-BuLi (2.5 M in hexanes, 2.0 mL, 4.9 mmol) was added drop wiseto the solution was stirred for 2 h at -78 C. After two hours, ethyl fluoroacetate (0.16 mL, 1.69mmol) was added drop wise and stirred for 1 min at -78 C upon which the mixture was then quenched with NH4Cl (20 mL) and warmed to room temp. The mixture was then extracted withether (50 mL), and dried over MgSO4. After concentration in vacuo (note: remove shortly afterthe ether is removed, because the compound is quite volatile), the residue was purified with flash chromatography over silica gel (hexane: ethyl acetate = 90:10) to yield the product as a yellowliquid in 43percent yield (0.12 g).

The synthetic route of 1-Bromo-3-(tert-butyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Camerino, Eugene; Wong, Dawn M.; Tong, Fan; Koerber, Florian; Gross, Aaron D.; Islam, Rafique; Viayna, Elisabet; Mutunga, James M.; Li, Jianyong; Totrov, Maxim M.; Bloomquist, Jeffrey R.; Carlier, Paul R.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 20; (2015); p. 4405 – 4411;,
Bromide – Wikipedia,
bromide – Wiktionary